Book Holiday Homes in Harpswell

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Featured Holiday Homes in Harpswell

Sunny Modern Oasis in Portland’s Trendy East End

Sunny Modern Oasis in Portland’s Trendy East End

Portland ME
Stay at this holiday home in Portland. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Portland Observatory and Maine Jewish ...
Opens in a new windowSunny Modern Oasis in Portland’s Trendy East End
Fantastic Waterfront Views

Fantastic Waterfront Views

Phippsburg ME
The price is NZ$643 per night from 20 Jan to 21 Jan
NZ$643
20 Jan - 21 Jan 2026
includes taxes & fees
Stay at this holiday home in Phippsburg. Enjoy laundry facilities and an in-room coffee maker. Popular attractions Bates-Morse Mountain Conservation Area and ...
Opens in a new windowFantastic Waterfront Views
Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Boothbay Harbor ME
Stay at this holiday home in Boothbay Harbor. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the property condition in their reviews. Popular ...
Opens in a new windowNewly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.
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Captain's Guest Room w/private bath. Walk to everything.

Captain's Guest Room w/private bath. Walk to everything.

Bath ME
Stay at this holiday home in Bath. Enjoy free Wi-Fi. Popular attractions Markings Gallery and Waterfront Park are located nearby.
Opens in a new windowCaptain's Guest Room w/private bath. Walk to everything.
Large, light filled 4 bedroom house - walk to ocean and ferry

Large, light filled 4 bedroom house - walk to ocean and ferry

Peaks Island ME
Stay at this holiday home in Peaks Island. Enjoy a garden, laundry facilities and patios. Popular attractions Umbrella Cover Museum and Fifth Maine Museum are ...
Opens in a new windowLarge, light filled 4 bedroom house - walk to ocean and ferry
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Boothbay Harbor ME
Stay at this beach holiday home in Boothbay Harbor. Enjoy a beach locale, a garden and laundry facilities. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowDowntown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock

Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock

Woolwich ME
Stay at this family-friendly holiday home in Woolwich. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Waterfront Park and Markings Gallery ...
Opens in a new windowWindward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock
Beautiful house on the Harpswell Peninsula over looking Casco Bay

Beautiful house on the Harpswell Peninsula over looking Casco Bay

Harpswell ME
Stay at this holiday home in Harpswell. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Mitchell Field and Paddleworks are located ...
Opens in a new windowBeautiful house on the Harpswell Peninsula over looking Casco Bay
Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

Scarborough ME
Stay at this holiday home in Scarborough. Enjoy a garden, laundry facilities and a pool table. Popular attractions Nonesuch River Golf Club and Maine Mall are ...
Opens in a new windowPrivate 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Harpswell Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Harpswell vacation homes are the perfect way for you to wing it.

Holiday houses in Harpswell let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Harpswell in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Harpswell adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Harpswell with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Harpswell vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Harpswell Holiday Homes essential information

Accommodation
608 Holiday Homes
Lowest Price
NZ$132
Highest Price
NZ$643
Popular accommodation
Sunny Modern Oasis in Portland’s Trendy East End, Fantastic Waterfront Views, Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH., Captain's Guest Room w/private bath. Walk to everything., Large, light filled 4 bedroom house - walk to ocean and ferry, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock, Beautiful house on the Harpswell Peninsula over looking Casco Bay, Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

Top trending hotels in Harpswell

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$162 per night from 24 Dec to 25 Dec
NZ$162
24 Dec - 25 Dec
includes taxes & fees
Stay at this business-friendly hotel in Portland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowClarion Hotel Portland Airport ME
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$188 per night from 6 Jan to 7 Jan
NZ$188
6 Jan - 7 Jan 2026
includes taxes & fees
Stay at this spa hotel in Portland. Enjoy free Wi-Fi, a full-service spa and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowThe Westin Portland Harborview
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star spa hotel in Portland. Enjoy free Wi-Fi, a full-service spa and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowPortland Regency Hotel & Spa
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Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road South Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$132 per night from 11 Jan to 12 Jan
NZ$132
11 Jan - 12 Jan 2026
includes taxes & fees
Stay at this hotel in South Portland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
Opens in a new windowTru by Hilton Portland Airport Area
Don't see what you're looking for?
See all available properties in Harpswell
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.